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Jamaica Vacation Packages

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Jamaica Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
Price was $407, price is now $402 per person
$402
per person
Apr 16 - Apr 18
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,068, price is now $977 per person
$977
per person
Apr 17 - Apr 19
found 24 hours ago
Roundtrip flight included
Sarasota (SRQ) to Springfield (VSF)
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $783, price is now $742 per person
$742
per person
Jun 5 - Jun 7
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Springfield (VSF)
Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bonnie's Bundles Dolls and DaVallia Art & Accents are located nearby.
The Vesper

The Vesper

3 out of 5
Price was $780, price is now $757 per person
$757
per person
Apr 17 - Apr 19
found 24 hours ago
Roundtrip flight included
Sarasota (SRQ) to Springfield (VSF)
Stay at this B&B in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Billings Park and Trail and Dana House Museum are located nearby.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $709, price is now $709 per person
$709
per person
Apr 17 - Apr 19
found 24 hours ago
Roundtrip flight included
Sarasota (SRQ) to Springfield (VSF)
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Fri, May 15 - Wed, May 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$131 Roundtrip, found 9 hours ago
$131
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Fri, May 15 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, May 27, priced at $131 found 9 hours ago
JetBlue Airways
Tue, Apr 7 - Sat, Apr 18
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$136 Roundtrip, found 11 hours ago
$136
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Tue, Apr 7 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Apr 18, priced at $136 found 11 hours ago
JetBlue Airways
Tue, May 12 - Wed, May 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$163 Roundtrip, found 9 hours ago
$163
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Tue, May 12 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, May 27, priced at $163 found 9 hours ago
Cape Air
Thu, May 14 - Mon, Jun 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 9 hours ago
$180
Roundtrip
found 9 hours ago
Select Cape Air flight, departing Thu, May 14 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 1, priced at $180 found 9 hours ago